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【结 构 式】

【分子编号】23569

【品名】(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

【CA登记号】

【 分 子 式 】C10H16

【 分 子 量 】136.23704

【元素组成】C 88.16% H 11.84%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

A) Synthesis of intermediate (IX): The reaction of alpha-pinene (I) with paraformaldehyde at 180 C gives 10-hydroxymethyl-2-pinene (II), which by reaction with dihydropyran and p-toluenesulfonic acid in dichloromethane is converted to the tetrahydropyranyl ether (III) The reaction of (III) with diborane in THF affords 10-(tetra-hydropyran-2yloxymethyl)pinan-3-ol (IV), which is oxidized with CrO3 - MnSO4 - H2SO4 in ether to the ketone (V). The stereoselective reduction of (V) with NaBH4 in methanol gives the alcohol (VI), which is mesylated with methanesulfonyl chloride and triethylamine in dichloromethane to the mesyl ester (VII). The reaction of (VII) with sodium azide in HMPT yields the azide (VIII), which by reduction with LiAlH4 in refluxing ethyl ether affords 10-tetrahydropyran-2-yloxymethyl)pinan-3-ylamine (IX).

1 Kawasaki, A.; Miyake, H.; Okegawa, T. (Ono Pharmaceutical Co., Ltd.); 13-Aza-14-oxo-TXA2 analogues. AU 8543495; EP 0171146; ES 8704880; ES 8705370; JP 1989151545; US 4792550 .
2 Castaner, J.; Prous, J.; ONO-3708. Drugs Fut 1987, 12, 5, 446.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 23569 (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene C10H16 详情 详情
(II) 23570 2-[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]-1-ethanol C11H18O 详情 详情
(III) 23571 2-[3-[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]propoxy]tetrahydro-2H-pyran; 3-[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]propyl tetrahydro-2H-pyran-2-yl ether C17H28O2 详情 详情
(IV) 23572 (1S,2S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]heptan-3-ol C17H30O3 详情 详情
(V) 23573 (1S,2S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]heptan-3-one C17H28O3 详情 详情
(VI) 23574 (1S,2S,3R,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]heptan-3-ol C17H30O3 详情 详情
(VII) 23575 2-[3-((1S,2S,3R,5R)-6,6-dimethyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]bicyclo[3.1.1]hept-2-yl)propoxy]tetrahydro-2H-pyran; 3-((1S,2S,3R,5R)-6,6-dimethyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]bicyclo[3.1.1]hept-2-yl)propyl tetrahydro-2H-pyran-2-yl ether C20H36O3S 详情 详情
(VIII) 23576 2-[3-[(1S,2S,3S,5R)-3-azido-6,6-dimethylbicyclo[3.1.1]hept-2-yl]propoxy]tetrahydro-2H-pyran; 3-[(1S,2S,3S,5R)-3-azido-6,6-dimethylbicyclo[3.1.1]hept-2-yl]propyl tetrahydro-2H-pyran-2-yl ether C17H29N3O2 详情 详情
(IX) 23577 (1S,2S,3S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]heptan-3-amine; (1S,2S,3S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]hept-3-ylamine C17H31NO2 详情 详情
Extended Information